Agent 355: The Mysterious Female Spy of The American Revolution

Oct 18, 2021 0 comments

Agent 355 sounds like a comic book character or the protagonist of a television series, but in reality it is the nickname of a real figure: a spy who acted during the American Revolution in favor of the rebels and who, therefore, could be considered one of the first people dedicated to that profession in the United States. The fact that her identity is not known for certain only adds to the historical interest of the matter, due to the theories that exist in this regard.

The curious thing is that hardly any testimony of her existence is preserved, which has caused rivers of ink to flow on the subject; not so much for its veracity, which is proven, as for the details that surround it all: if she was an agent properly speaking or just an occasional collaborator, if she belonged to a family of illustrious lineage, if she really had the sad end that the legend tells... These doubts derive from the scarcity of sources, since the only express mention that is made of Agent 355 is in a letter sent to George Washington.

Agent 355, as depicted in an 1863 issue of Harper's Weekly

The future president of the United States was at the time general-in-chief of the Continental Army (named after the First Continental Congress, held by the revolutionaries in 1774) and from the first moment he had understood the need to create an intelligence service to counteract the theoretical British military superiority. Hence, he recruited dozens of agents for espionage and counterintelligence missions. He himself gave them instructions in letters in his own handwriting, indicating that he preferred to receive the information in the same way to save time and ensure that they were not discovered.

Washington sought and obtained funds from the Continental Congress for this secret service, opting to receive them in cash, preferably in gold ("I have always found it difficult to get intelligence through paper money," he said). In accounting for the sums in his diaries, he did not identify the recipients because, in his own words, "one cannot include the names of persons who are employed within the enemy's lines or who may fall into his power." In this connection, he encouraged his officers to spare no expense and to assign to espionage work those "on whose firmness and fidelity we may safely rely."

Some of Washington's collaborators in that field are well known: Joseph Reed, his right-hand man and organizer; Alexander Hamilton, in charge of receiving the reports and discovering a double agent (he would later become the first US Secretary of the Treasury); Elias Boudinot (not to be confused with the famous Cherokee journalist), commissary general of prisoners and in charge of coaxing information out of them; Charles Scott and David Henley, who succeeded each other as intelligence chief, until they were replaced by Benjamin Tallmadge, the organizer of an espionage network in New York; Thomas Knowlton, who headed an operational unit in the field (Knowlton's Rangers); and several others.

Portrait of Benjamin Tallmadge with son William, 1790

They commanded field agents, among whom may be named the pioneering (and ill-fated) Nathan Hale, Haym Salomon, Abraham Patten, James Rivington, Hercules Mulligan, Lewis J. Costigin, and Dominique L'Eclise. But there is only one reference to Agent 355—a letter that Washington received from Abraham Woodhull. This was the son of a wealthy landowner who resigned his post as lieutenant in the New York Suffolk County militia when the British captured his cousin, General Nathaniel Woodhull, who was seriously wounded and left to die without medical aid or food. It turned out that Benjamin Tallmadge, whom we mentioned earlier, was a neighbor of his and recruited him to the cause, incorporating him into the network of spies he was organizing.

Woodhull took up residence in a boarding house run by his sister in Manhattan, where British commanders and officers often stayed. He began to supply information in 1778, sending correspondence—which he signed with the nickname Samuel Culper—by means of the whaling boats of another member of the network, Samuel Brewster, a direct descendant of one of the Mayflower pilgrims. As a signal for the two to contact each other, a neighbor, Anna Strong, hung a black petticoat on the line, indicating the exact location of the delivery with a code of handkerchiefs, also hung. In this way, Washington obtained valuable information about, for example, the barges that the Royal Navy built to transport troops or to practice privateering.

Specifically, the letter alluding to Agent 355 was signed as Samuel Culper Sr (Woodhull's usual pseudonym) and described her as "one who has always been of service to this correspondence". That's all; enough to let Washington know that he had recruited a spy in his service in New York, but not enough to know her identity. However, there is no lack of speculation about her, and the first is to suppose that it was the aforementioned Anna Strong.

Anna Smith, her maiden name, was a neighbor and Woodhull's collaborator. She was born in 1740, daughter of a colonel and granddaughter of a judge, marrying Selah Strong—from whom she took her surname, who was a delegate in the first three New York provincial congresses (provisional governments constituted between 1775 and 1777 to replace the Committee of Sixty, which the rebels formed to put into practice the boycott of British commercial interests), as well as captain of the New York militia.

In January 1778, Selah Strong was arrested and imprisoned on the HMS Jersey, a fourth class ship of the line which by that time had become obsolete and for that reason the Royal Navy assigned it first as a hospital ship and then as a floating prison, anchored in Wallabout Bay, near Long Island. Captured rebels were held there, living in very harsh conditions, crammed by the thousands in a space designed for four hundred, with hardly any air circulation, little health care and very little food. For this last reason, it was not uncommon for their relatives to visit them from time to time to bring them food.

HMS Jersey Prison Ship

Anna was not only one of those who did so, but she managed to get her well-to-do and conservative relatives to pressure the authorities into releasing her husband on parole. Once free, it was deemed advisable for Selah and her children to get out of the way, settling in Connecticut, while Anna remained in the family home on Long Island, since British law provided for the confiscation of her land if it was abandoned.

It is likely that Anna was the woman Woodhull referred to in another missive, in this case sent to Benjamin Tallmadge, in which she announced that she was traveling to New York and that "with the help of a [lady] I know, I will be able to outwit them all [the British]." It was around the time she was going to Wallabout Bay to bring food to the imprisoned Selah, a perfect cover that was thickened by the peace of mind provided by her family being considered trustworthy by the enemy, all of which could be indicative of her identification with Agent 355.

If true, the money given to Selah Strong for expenses, as listed in a George Washington item, would correspond more to the activities carried out by the beneficiary's wife, given that he spent most of his time incarcerated on HMS Jersey. However, not all historians are convinced that Anna was Agent 355 and recall that there was at least one other lady (that is what the number 355 meant in the cipher code used by Woodhull), probably upper class, infiltrated among the British commanders.

There is no information about her either, but it is known that she was part of the circle of friends of Major John André, appointed head of the British secret service in the American colonies in 1779, after having gone through the odyssey of falling prisoner of the rebels and being released in an exchange. Apparently, André liked to lead a dynamic social life, surrounding himself with young women whom he attracted with his good looks, sympathy and culture (he drew, sang and was a prolific writer, both in prose and verse, in addition to speaking several languages). Peggy Shippen was one of those who fell under his charms, when he made an orientalist portrait of her wearing a turban.

Peggy Shippen and her daughter

She was the wife - very young, only sixteen years old - of Benedict Arnold, an American general who, after some personal problems and disillusioned with the fall of Philadelphia, was considering going over to the enemy side in exchange for a generous amount of money. It was Peggy who put her husband in contact with André so that they could negotiate the surrender of the fort at West Point, which was under his command; something that would have allowed the British to isolate New England. They agreed to a personal interview, but the British sloop was discovered and he was forced to flee overland in disguise.

He was unsuccessful; intercepted by two soldiers, a court martial sentenced him to death in 1780. André did not give Benedict Arnold away, but the papers he was carrying did. However, what is often considered the first traitor in U.S. history was able to escape thanks to his wife, who after all was the originator of it all, who gave him time by feigning a fit of hysteria and fainting before Washington when he and his men came to their house to arrest him.

Earlier, Arnold had questioned André's entourage because he suspected that the whole thing had been a deliberate trap and he noticed a woman who might be Agent 355; the suspicion was due to the fact that she was pregnant and refused to give the name of her lover. He denounced her to the British, who imprisoned her on the HMS Jersey, where she died, but not before giving birth to a son whom she christened Robert Townsend Jr. In fact, not only is there no record of any birth on that pontoon, but there is no record of any female captives on board. But the legend attributes an obvious paternity to that child: that of the man who bore his same name.

Benedict Arnold

And he was none other than Robert Townsend, just another agent Woodhull had in New York. Born in 1753, son of a Quaker and an Episcopalian who had a thriving store, he decided to join the patriots both because of the influence of reading Thomas Payne's Common Sense and because of the tax pressure from the metropolis and the pillage suffered by the population of Oyster Bay at the hands of the soldiers, something from which his family was not spared (the Queen's Rangers occupied their house as lodging for the officers). The faith he professed, however, prevented him from taking up arms, so his friend Woodhull offered him to join the so-called Culper Ring.

The Culper Ring was the name given to the spy ring created by Tallmadge and Woodhull in New York. Culper was a reference to Culpeper County and it was apparently Washington himself who proposed it remembering the place where he had worked as a surveyor in his youth, Woodhall assuming the code name of Samuel Culper Sr. and Townsend that of Samuel Culper Jr. while Tallmadge used that of John Bolton. Townsend became the principal agent in the field, as his friend was beginning to become too well known to the enemy, and remained as intermediary supervisor between him and Brewster.

Their respective sisters were also part of the circle and played a prominent role in the alleged frame-up of John André. We have already seen that Woodhull's Mary Underhill had the cover of the boarding house; Townsend's Sarah (aka Sally), born in 1760, was the one who reported André's plan to bribe Benedict to obtain West Point, something she overheard him discussing with General John Graves Simcoe of the Queen's Rangers when they moved into his house. Simcoe was courting Sarah, who was then around eighteen, and it is possible that she agreed to have a brief relationship with him that allowed him to learn all about it. However, the romance did not prosper and he married upon returning to Britain while she remained single for the rest of her life.

A page from the code book of the Culper Spy Ring during the American Revolutionary War. On the left of the page are the names of people and places side-by-side with numbers that serve as their code representations.

It is likely, however, that all, or part of it, is simply a legend, since the details do not fit: the soldiers left the Townsend home in the spring of 1779, so the general could not have devoted more than a couple of months to Sarah, and the half-romantic, half-spy story did not begin to be told until a century later. But the rest is true and Robert Townsend, who provided much valuable information, managed to keep her identity secret even after his death in 1834; it was not discovered until 1930 and the controversial family home is now home to the Raynham Hall Museum.

Was Sarah Agent 355 or was Anna Strong? Impossible to know because there is still a third candidate, Elizabeth Burgin. Even less is known about her than about the others, although some information is common: widowed and mother of three children, she used to take food to the prisoners on the pontoons and that is why in 1779 George Higday, another Culper Ring agent, approached her, proposing to join the cause and help her in a project to escape from the prisoners. Soon after, that summer, the British intercepted a letter from Washington to Tallmadge in which he mentioned Higday, who was immediately arrested.

His desperate wife decided to help him by denouncing Elizabeth and the authorities offered a reward for her capture. After remaining in hiding for two weeks, she moved to Long Island, where she stayed for a month before moving on to Connecticut and from there to Philadelphia. When autumn arrived, a truce was signed that allowed her to recover her children, although she was in ruins and so Washington assigned her a pension that she received, according to the archives, at least until 1787.

The mystery of Agent 355 remains.

This article was originally published in La Brújula Verde. It has been translated from Spanish and republished with permission.


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